


An Unnecessary Lesson

by 0xenfree



Category: Supernatural
Genre: Alternate Universe, Alternate Universe - High School, Alternate Universe - Modern Setting, Best Friends, Blow Jobs, First Kiss, First Time, First Time Blow Jobs, Fluff, Fluff and Smut, Friends to Lovers, Hand Jobs, High School, Lingerie, M/M, Making Out, Naked Cuddling, Sam Winchester Knows, Smut, Women's Underwear
Language: English
Status: Completed
Published: 2020-06-22
Updated: 2020-06-22
Packaged: 2021-03-04 03:34:47
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,453
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24866917
Author URL: https://archiveofourown.org/users/0xenfree/pseuds/0xenfree
Summary: Why did they think this was a good idea? To make a short, stupid story even shorter, Dean was now standing in the hallway with his younger brother trying to take a hot pink bra off of him, and his best friend staring right at them.Dean tries to be a good older brother and help Sam out, but it turns out that that never goes well for him, does it?
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester, Dean Winchester & Sam Winchester
Comments: 5
Kudos: 98





	An Unnecessary Lesson

**Author's Note:**

> Look at this! I'm alive!
> 
> I know it's been a while since I've posted something, probably a year or so at least, and for that, I'm truly sorry. I dug up an old notebook from last Summer that had about 3 fics-worth of content, so I'm finally typing it up and posting it now.
> 
> Fun fact: This is based on a true story told to me by my friend, but slightly edited to fit the characters. In the original story, he walked in on his girlfriend's brothers in Dean and Sam's situation.
> 
> I have one Good Omens fic to post and two more Destiel that I want to post. After that, I don't know, but I remembered an old concept that I think I'm going to change into a Check Please! Zimbits fic. I have some other old lists and concepts and half-finished writing that I may work on as well, so stay tuned!
> 
> Again, so sorry for dropping off of the face of the earth for a while, I promise I'm still around :)

Why did they think this was a good idea? To make a short, stupid story even shorter, Dean was now standing in the hallway with his younger brother trying to take a hot pink bra off of him, and his best friend staring right at them.

Sam, being the 13-year-old that he was, decided that he needed to know how to unhook a girl’s bra. Of course, he enlisted the help of his older brother, who just so happened to have one of Charlie’s bras in his possession from when she accidentally left it at their house after sleeping over. Dean, being the good older brother that he was, reluctantly agreed to put it on and show Sam how to get it off.

What they hadn’t thought of was the fact that Charlie was much smaller than Dean, and in their struggle to get it on him, they broke the clasps and got it stuck. As if the situation couldn’t get any more embarrassing, Castiel had shown up at that exact moment. Dean had invited him over earlier, and since he knew that the door was always unlocked while the boys were home, he had simply walked in. The sight that greeted him was quite unexpected.

Castiel stared at the pair of brothers, unblinking and not speaking. “Um-” he began, “Dean?” The blue-eyed boy tilted his head to the side, clearly trying to figure out what the hell had happened here.

“Heyyy Cas…” Dean cringed at how his voice cracked and how awkward he sounded. This wasn’t exactly how he’d hoped for his best friend and long time crush to ever see him shirtless and wearing women’s undergarments. Not that that was something he’d ever wanted in the first place…

Sam thankfully broke the awkward silence and subsequent staring contest with a loud clearing of his throat. “Cas, care to help?” He took his hands off of the clasps, lightly shoving Dean towards Castiel. “Oh, and you might want to go to Dean’s room, in case someone else decides to show up.” Dean shot Sam a glare, but the younger Winchester just grinned back evilly. Dean thanked his lucky stars that it all went over Castiel’s head, still too distracted by what was going on in front of him. Either way, the pair of 17-year-olds made their way to Dean’s room, closing the door behind them.

They stared at each other for a moment before Dean spoke, breaking the silence. “Gonna help me out here?” He gestured to the bra. Castiel was also now realizing that it was not only pink but decorated with lace as well. It was clearly too small for Dean and stretched a bit awkwardly around his ribcage, but the pink contrasted nicely with Dean’s skin, Castiel thought. He noticed small smatterings of freckles dusting Dean’s shoulders, something he’d never noticed before.

“Yes, uh, right,” Castiel stammered. “Um, turn around? And I’ll try to get it off.  
Dean nodded once, turning his back to Castiel. He felt Cas step up behind him and place his hands on his back. Cas’s hands were warm and his fingers tickled his back where they touched him. _Much more gentle than Sam_ , he thought idly.

Castiel looked closely at the clasps, touching Dean a bit more than was probably necessary. The boy did have a very nice back though, and the close position they were in could easily be turned into something sexual. He knew immediately that this moment would become a memory to feed _many_ future jack-off sessions. He had to control himself though, now was not the time or place to be getting hard over Dean Winchester.

Finally, Castiel saw the problem. The fabric had gotten stuck beneath the clasps, making it incredibly hard to unhook them. Though, he wasn’t even sure how the boys had even managed to get it stuck like that in the first place. Leave it to the Winchesters, he supposed. 

He tugged at the stuck clasps, pulling hard enough to cause Dean to become unsteady. After a minute of working at the clasps, Castiel finally got it unhooked with a final harsh tug. However, the motion knocked both boys together, Cas’s front pressed to Dean’s back. In their mutual surprise, instead of catching themselves, they fell to the floor. Dean had tried to overcompensate for falling backward and instead ended up pulling Cas forwards with him, landing with Castiel on top with Dean on the floor beneath him.

To make matters worse, there was a clear hardness in Cas’s pants since he hadn’t, in fact, been able to stop thinking about Dean. He knew Dean could feel it too, because he’d tried to push himself up but accidentally ground against Cas’s dick, causing the boy on top to let out a surprised gasp. Was this some kind of karmic retribution for his sexual thoughts about his best friend? Must be, Castiel reasoned.

Now though, both boys were still. Neither moved, in fear of making the situation worse. However, they couldn’t stay there either, and Castiel was on top so he had to move first. He pushed himself up on his hands and knees, only groaning a little bit when he brushed against Dean’s ass. He was expecting to stand up and have neither of them talk about it ever again, but before he stood, Dean flipped over to face him. The bra was still on for the most part. Dean licked his bottom lip nervously, and Cas had the intense urge to kiss him right then and there.

“Cas,” Dean whispered quietly. He swallowed thickly, licking his lips again. He spoke shakily, “Wanna help me out with this?” He glanced down at his chest when he asked the question. 

The air between them felt thick with tension as the boys watched each other. Cas’s mouth felt dry as he slipped his finger beneath the band of the bra, trailing it over Dean’s chest from one side to the other. He then slid his hand under the cup, trailing his fingers and palm over Dean’s nipple. The green-eyed boy inhaled sharply, his pupils dilating further.

Cas hooked his fingers under one of the straps of the bra and worked it off of Dean’s arm, then the other, pulling it off completely. Neither of them spoke or signaled for anything, but neither pulled away either as Castiel bent down and pressed his lips to Dean’s. They kissed close-mouthed for a few seconds, processing the shock of what was happening. Soon though, the dam broke as Dean ran his tongue along Cas’s lip.

The kneeling boy opened his mouth and let Dean’s tongue inside, sucking gently. They stayed in that position, kissing and licking into each other’s mouths, for a while, hardly moving aside from Dean’s hands coming up to rest on Cas’s waist.

A minute longer and Cas finally lowered his weight onto Dean, pressing their hips together. They pushed against each other, grinding together through their pants. Both boys were letting out small, pleased sounds, feeling no need to hide them from each other.

Eventually, Dean pressed his hand on Cas’s chest, pushing him upward. “Cas, bed,” He whispered against the other boy’s lips. Cas simply nodded and stood up, pulling Dean with him by the hand. Cas sat down on Dean’s bed, expecting the other boy to seat himself beside him; however, Dean chose instead to straddle Cas’s thighs, their faces coming to a hair's breadth apart.

“Shit, is this okay?” Dean asked upon seeing Cas’s started expression, a look of worry in his eyes. His eyebrows were slightly creased and he had a small frown tracing his lips, a look which Cas immediately wanted to resolve.

“Oh, um, yes, this is okay.” Cas blushed as he stammered out a response. Dean let out a small sigh of relief, giving Cas a gentle smile before leaning forward to capture his mouth again. Castiel let out a small moan as he felt Dean’s lips reconnect with his, and his hands moved to grip the Winchester boy’s thighs.

Dean smiled against Cas’s lips when he felt the other boy’s hands on him and threaded his own hand through Castiel’s hair. The first thing he noticed was how soft it felt.

He pressed his body closer to Cas’s, beginning to rock his hips gently against the other’s. Dean loved the sound that his motion drew from Cas, both feeling and hearing the gasp and hitch in his breath.

Cas moved his hands lower, gripping Dean’s ass a bit too harshly to be gentle, and hauled the boy even closer to him, if at all possible. The two boys were pressed against each other as much as two people could possibly be, and yet it still didn’t feel close enough. Cas ran his hands up Dean’s sides with a full range to run his hands along Dean’s chest, back, and stomach. His whole body felt warm and smooth, and Castiel loved how he felt beneath his palms. He wanted to know how the rest of Dean would feel under his hands...

Between their kisses, the boys worked so that they were positioned properly on the bed instead of simply sitting on the edge. Dean was laid on his back with Cas hovering over him, legs spread and straddled over Dean’s. As they continued to kiss, Castiel let his hands trail down from Dean’s chest down to his jeans, where he could feel a hardness forming a bulge. 

Cas pressed his palm down against Dean’s erection, drawing a sharp inhale from the boy. He rubbed over the rough denim of Dean’s jeans, teasing him with his fingers. “Cas,” Dean moaned out breathily, “Stop teasing.” Dean pouted slightly with lust-filled eyes, and it was the most breathtaking thing Cas had ever seen.

So, he complied and worked to unbutton and unzip Dean’s jeans. He looked up at the green-eyed boy, asking “Is this okay?” With an enthusiastic nod from the boy, Cas smiled and worked Dean’s pants down his legs. With them off, it was easy to see the obscene tenting of Dean’s boxers, as well as a small damp spot near the waistband.

Cas ran his fingers along Dean’s hardened length, teasing with one finger at the tip. When Dean let out a whine, Cas finally tugged Dean’s boxers off as well. While it was one thing to feel Dean’s boner, it was another entirely to see it as well. His dick was flushed a warm pink at the head and curved slightly up towards his stomach.

When he reached down to grasp it in his hand, Dean gasped and sighed once more. Castiel stroked him gently, gripping from the base and sliding upward a few times. He could see a small pearl of precum beading at the head and leaned down to lick it off, reveling in the startled gasp and moan that he caused. 

He slid his mouth down Dean’s length, sucking on the head as he came back up. He licked along the bottom vein, putting more pressure beneath the head just to hear Dean whine. Allowing his mouth to provide more spit as lube, he took Dean back into his hand and stroked him faster than before.

He watched Dean’s leg muscles tense and looks of pleasure play across his face. Castiel was entranced by Dean’s twitching stomach muscles and his fingers tightly gripping the sheets as he touched him. As soon as he felt the spit drying, he replaced his hand with his mouth and bobbed his head.

He sucked Dean for a while more before returning back to his hand. Dean caught his eye before moaning out, “Cas, wanna feel you too.” Cas felt himself grow warmer when he heard how wrecked Dean’s voice was. Keeping one hand on Dean’s cock, he quickly tried to release himself from his own jeans and get a hand on himself.

Cas hissed in pleasure when he brought both his and Dean’s cocks together in his hand. Dean wrapped his hand on top of Cas’s for a moment as well, wanting to feel them pressed together. Castiel stroked both of them together, slowly going faster as they both approached the edge. While he started later than Dean, he had become quite on edge as he played with the boy beneath him.

Soon, Dean was moaning out beneath Cas. “Fuck Cas,” he gasped, “‘m gonna cum.” Cas only nodded in agreement as he felt Dean start to pulse and release on his hand. Watching Dean cum on his hand and cock was just enough to push Cas over the edge as well, spilling over his hand and onto Dean’s stomach, both of their messes mingling.

Castiel caught his breath for a moment before looking for something to clean them up with. He kicked off his jeans and boxers as he stood, trying not to trip over. Decided on a sock laying on Dean’s floor, not the nicest but available, he worked on cleaning them up. As he wiped off his hand and moved on to Dean’s stomach, their gazes caught each other. Dean offered a small, pleased smile that Cas returned.

Dean patted the space next to him in an offer to Cas, who quickly dropped the sock he was holding and crawled up next to Dean. The green-eyed boy plucked at Cas’s shirt, muttering, “Take this off. Wanna feel you too.” Castiel was happy to comply and quickly tugged off his shirt before laying down next to Dean.

The Winchester threw one of his legs over Castiel’s, and in return, Cas wrapped his arm around Dean’s chest, resting his cheek on Dean’s shoulder.

“That was nice,” Dean said softly, brushing his hand over Cas’s bicep and shoulder. Cas closed his eyes and nodded in agreement. “Didn’t know you wanted me like that,” Dean whispered against Cas’s hair.

Cas picked his head up and looked Dean in the eyes. He took a second to admire the boy’s beauty before speaking. “How could I not?” Castiel asked, a small frown gracing his features. “I’ve only ever wanted you…” He added, blushing and glancing away. Dean bit his lip, holding in a small smile. 

“Me too, Cas. Wanted you for a while now,” Dean said, his own face turning slightly pinker. When Cas looked back up at him, Dean couldn’t help but drop his head down for a kiss. He smiled against Cas’s lips, and when he drew back, Cas subconsciously chased his lips for a second.

The two boys smiled at each other and Castiel dropped his head back to Dean’s shoulder. Both were content to not say any more. They didn’t need to say more, they understood each other perfectly.

**Author's Note:**

> Thank you so much, dear reader, for taking the time to read this!
> 
> Of course, comments and kudos are appreciated! And let me know of any errors or mistakes :)


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